Escort
- 2 years ago
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I shall start my introducing myself. I am a 30 year old woman who earns
her living dressing males as women. Usually they end up dressed fully by
which I mean from the skin out (undies) skirts and tops or perhaps a
dress. Cosmetics and high heels in that case may be taken as a given.
Some of the clients make pretty ugly women but yet more turn out as
reasonable women and a small number look very much the part. I don't allow
then to have them penetrate me however I am open to being pleasured with
their tongues and most want me to use a strap on dildo on them.
I met my partner through work as it were. She, well he was the correct
pronoun at the time came to avail of my services one winters evening. He
was ever so nervous and one of the first things that I noticed about him
was how naturally feminine he was even when dressed as a male.
Initially things went as usual, which is that you sit and talk with the
client, putting them at ease, then work out what they really want and find
out what experience they have of dressing as a woman.
We sat and chatted for a while longer than usual as I as quite taken by
him. He took a little while to open up to me however when he did he told
me that he actually wanted to be a woman. You come across them from time
to time but even now he is the one that was the most creditable. I
finished with asking him if he had a woman's name that he used, he did,
and his female persona was Paula
Having established that he wanted to both dress fully and he used as woman
sexually I determined his clothes sizes and asked him to shower. From that
point in this tale I only called him or rather her Paula. She undressed
and I could see that she was already wearing panties and had kept her body
clean shaven. I turned my attention to sorting out the clothes that she
was going to wear. Black lacy panties and a bra were a must, large breast
forms and naturally stockings. I looked up at that stage and watched her
shower. She was so feminine about it, clearly not forced or pretending, I
realized that this session would be different for any one that I had done
previously. Looking at her I surprised myself at the heat building between
my legs and my nips getting hard. I had never been sexually aroused by
what I do previous to that evening. Dragging myself back to the task in
hand I looked through the wardrobe and I picked out a short black skirt
and plain white silk blouse with a white dress as a backup if she did not
want to wear the skirt and blouse or they did not suit her.
She had finished showering and had dried herself off by this stage and
appeared before me with a towel wrapped around her with one end tucked in
between her chest - just like a girl. I eyed her up and asked him if she
was ready for have her face had up. She nodded a yes. Her face was
already clean and ready for makeup so I was able to get right to work.
First off was a base of concealer which I spread across her face evenly
and worked in. Next I got to work on her eyes, mascara and eyeliner. I
used dark mascara on her long lashes and dark blue eye liner. Blushers
followed and then lip liner and finally lip stick in a light red colour. I
asked Paula is she would like some perfume. She asked to sample what the
perfumes I had and picked one which oddly enough is one that I use myself
from time to time.
I then offered Paula the choice of dresses or the skirt and blouse
combinations. She picked out the skirt and a white satin blouse, a match
that would be quite acceptable in an office environment. I handed her the
panties which she slipped on without removing the towel - very feminine
behaviour! Next was her bra which she was able to put on and clip closed
with no assistance from me. Handing her the breast forms she slipped then
into the cups of her bra and promptly adjusted the straps just like a
generic woman would. Clearly she had a lot of practise. It took me quite a
few months as a teenager to be able to master those skills. The stockings
went on next and finally the blouse and skirt. A pair of low heels was
that last touch and a quick refresh of her perfume and she was fully
transformed. I noticed that she did not get erect and not only that when
she pulled her panties up she casually tucked her cock back between her
legs.
The sight of her added to my sexual excitement which was somewhat
embarrassing and I found it hard to professional about all of this but I
was looking at a very attractive and feminine woman. Normally at this
stage with a client I would either move on to what they want - be that
penetration with one on my dildos or whatever else they asked for, Some of
my clients, the true transsexuals like to sit and talk and Paula was no
different. We sat and talked for the rest of the booking and when her hour
was up she asked to stay and pay for another hour which as I did not have
another booking for the evening I was more than happy to agree to. As we
talked her history as it were of wanting to be woman came out. She knew
she wanted to be female at an early age and had only sisters who let her
wear their old clothes. A loner in some ways and she played with her
sisters toys rather than boys toys- all very classic signs of her gender
issues. Half an hour into the second hour we kissed - a first for me with
a client and moved on from there. I took the lead and had my tongue down
her throat. I had been with women before as well as men and it was obvious
that Paula was very much a woman. We did not go any further that evening
and at the end of the second hour she had to leave. She undressed removing
her makeup and got dressed back in what she wore when she came to see me.
I checked her makeup removal for any remaining evidence of it as I do
normally with clients.
As she was about to leave she asked me if I would be interested in helping
her shop for clothes which I was more than happy to do so. I was really
delighted that she asked me and I told her that I would be delighted to do
so and that it would be for free. We arranged to meet two days later and
with that she left.
After she left I was still very turned on by the last few hours and I just
had to relieve myself. I took my own blouse and skirt off and lay back in
a comfortable chair. My hand found its way in to my panties- I was very
wet and my clit was hard. I shut my eyes and pictured Paula in a
miniskirt, her breasts on display in a shelf bra kneeling between my legs
licking my pussy. I started to pleasure myself and in a surprisingly quick
time I came. I should add that I am one of those women who squirt and I
most certainly squirted that tine.
The next two days really dragged on. Paula was always in my mind. I was a
little disturbed by that truth be told as I had a rule about keeping a
distance between myself and clients but somehow she had gotten right
through my defences. The great day came at last and I took some time
getting ready, taking a long shower and using a little more makeup than
usual. I wore a delightfully white Basque and thong, a white silk blouse
and black skirt and 3" heels with stockings. We met as agreed in a coffee
shop in a local mall. Paula had an arrived early and looked ever so
nervous. We hugged and as we did so I could feel the lines of a bra. I was
pretty sure that she was going to be wearing at least panties and a bra
which she was however she was also wearing women's jeans and a top that
was feminine but not overtly, a style which suited her. We had our coffees
and as we drank them we talked about what she wanted to buy, what styles
would suit her and what she already owned What she was seeking was very
much a normal woman's wardrobe and not the slutty look that some cross
dressers or novice transsexual women pick. Here was yet more evidence that
not only was she for real a transwoman but that she had both a lot of
experience at dressing as a woman and had worked out her look. God knows I
long it took me, a natal woman years to get that right!
Finishing our coffees we went first to a lingerie store as Paula wanted
some padded bras, panties and camisoles. Shopping with her reinforced
again just how female she was and the fact that she was not, well not
physically anyway just disappeared from my mind. She picked out two
double padded bras, one in white and the other in red. I was curious as to
why she wanted A cups rather than a bigger size. Her explanation was that
she was preparing for the time when her started hormones and would been to
wear a bra so a small cup would be what she needed. They also had padded
panties in the shops shape wear collection which would do a good job
keeping her flat between her legs and help give her butt the right look.
She asked me if I would like anything and I surprised myself by suggesting
a baby doll nightdress. They had a most wonderful one in my size in power
blue. Paula being the sweetie she is added that to her collection. We went
to the check out and she had no signs of being embarrassed paying for her
items. Leaving the store we moved on to a upmarket boutique where I knew
that an old friend and sometimes lover Emma was working that day Entering
the stop Emma spotted me and came over. I introduced Paula by name and
then took Emma aside and explained all. I knew Emma would be cool with
having Paula try on clothes as it was both early in the day and that her
sister had been born male and had her final surgery the year before. As I
was explaining all to her I could see that she was eying Paula with a view
to styles that would suit her.
We walked back to Paula and Emma took her by her hand and asked her if
there was anything in particular that she would like to try on. Paula's
was a little bit taken aback by being addressed as Paula and being treated
like any other woman. She got over it quickly and pointed to a long light
brown skirt with white trimmings and then to a beautiful blue knee length
dress. They were quickly quite engaged in what they were doing which gave
me the opportunity that I wanted to go back to the lingerie shop where I
purchased a matching baby doll nightdress to the one Paula bought me but
in white.
Back to the boutique I went to see Paula disappear into a changing room
with an arm full of skirt tops and dresses. As she changed into the first
outfit Emma commented on hoe feminine Paula was and that she would have no
problems passing as a woman and that if she wanted to go further and have
surgery that she was blessed with a body that was already half way there.
Emma had noticed that Paula had wider hips for a male, narrow shoulders
and a butt that once filled out a bit would look just right in a skirt or
women's jeans.
Paula came out of the changing room wearing the skirt that she had first
spotted and a white top. The outline of her bra was very obvious, oh well
something for her to learn, black bra's stand out quite a bit! The top
looked well with the skirt and did suit her however we both pointed out
that she would need a camisole with the top. Paula looked in a long mirror
and spotted the issue. We both reassured her that all was well and not to
worry about it. She spend a bit of time admiring herself in the mirror,
enough to earn a loving smack on her butt to go and try one more things.
She went through her initial selections. Some looked well and others not
at all. Once done with that selection and I guess with all of us having a
better eye for what suited her we did another browse around the racks
picking out more dresses. This time around they all look good on her,
particularly a plain black number. We spent a good two hours at this and
at the end of that Paula had picked out two skirts, four tops and two
dresses. She paid for them, they were expensive but good quality and would
continue to fit her if she started hormones as I was sure at the time she
would.
With our shopping trip completed I invited her back to my home which she
accepted. Back hone I suggested that she get changed into something that
she had bought. I did not have to ask her a second time and she asked me
if she could borrow a camisole. I agreed and in my bedroom she changed.
Stripping fully she put on one of the super padded bra's matching panties
and a camisole that I offered her. Looking at her in the lingerie there
was little male on display with the padded panties doing a very good job
flatting her down there. I asked her about some makeup and she looked at
me and asked me if she could try putting her own face on as she phrased
it- very girlie I must say. I agreed and watched as she used my cosmetics.
She did a decent job of it, a tab too much for my liking and that she
needed but then again quite a few women wear a little too much for my
liking. Once done she asked me what I thought of her efforts. I told her
and had a little touching up to do one her mascara. She seemed very
pleased and before she put her skirt and top on I handed her some breast
forms that I had bought for `work' but never used as none of my clients
seemed into be interested in having small breasts but as Paula was wearing
an A cup bra they fitted perfectly. She slipped them into the cups of her
bra and moved them around so they looked correct. She put her skirt and
top on and then turned to check herself out in my long mirror. I must say
that she looked her much a woman and a rather pretty one at that.
We talked the rest of the afternoon and evening. I wanted so much to get
her to go out with me dressed as she was for dinner but I knew that I was
too early for her to do that. It was about eight in the evening when she
told me that she had to leave which made me ask her why and suggest that
she stayed the night. Her reason was that she had to work the next day and
had an early start. I suggested that she stay and that we could get up
early and I would drive her home. I could see that she was between two
minds. Stay or go? I reached forward and kissed her, moving one hand to
one of her breasts. She succumbed to my advances and we were deep in a
tongue kiss, hands of each other's breasts. Moving back to my bed room we
undressed each other down to our panties and bra's I asked her to keep her
bra on and breaking free of our embrace I found the baby doll that I
picked out for her. She was very pleased with the present and put it on as
I put my matching nightdress on as well after removing my bra.
We had a wonderful night of love making, using vibrators and dildos on
each other and her tongue on me Paula was a natural behaving like a woman
sexually and a submissive one at that. That night was when I started to
refer to her body parts in female terms. I don't have to explain what I
mean by that. I also got her to use the same terms.
Our relationship really started that night and we were seeing each other
initially two maybe three times a week. The same pattern every time, she
came to my home and got changed. Her makeup skills improved and did her
mannerisms and what not. I guess I was educating her in regards to being a
woman, refining how to she walked and all the other things in a female
manner. She told me that it was starting to affect her when she was
dressed as a male with her getting comments from people at work. The
comments were it appears all from women and by and large supportive.
Little did they know that each and every day Paula was wearing panties to
work.
I was getting somewhat bored with just staying at home with Paula and I
talked her into going out for a meal some distance away. It took me time
to get her to agree but eventually she did. We spent extra time on her
makeup that evening to get the look just right. She wore the plain black
dress that she liked so much and low heels and stockings. The restaurant
was some distance and when we go there she was calm and collected when we
entered. The waitress came over to us and we were seated straight away. As
we browsed the menu I noticed that Paula's face had gone white and I heard
a very naughty word out of her mouth. I look at her and asked her what was
wrong. She told me that two women from her office where here. I glanced at
where she indicated they were sitting. There was two young women sitting
at the table she indicated and it was very obvious to me that they were
more than just friends. I pointed that out to Paula and suggested that not
only were they highly unlikely to recognise her, they were not likely to
have an issue. We ordered our starters and then the main. Chatting away
Paula calmed down and all was well, she had put the other women out of her
mind, so much so that when they when stood up to leave neither of us had
noticed. They to walk past us not saying anything to us or even paying and
attention.. We ordered some coffee and while waiting for the coffees we
went to the ladies restroom. This was a first for Paula however she seemed
confident enough. We were the only two in the rest room when we entered
and I good naturedly reminded her to wipe front to back. We both did what
we had to do and washed our hands. I took my lipstick out of my handbag
and touched up my lips which reminded Paula to do the same thing. Once
finished we returned to our table to enjoy our coffees.
On our way home we discussed the evening and how it went. Paula was on a
high. First time out in public as a woman and it went well. Not only that
but she was in the same place as two people she worked with who did not
recognise her and she had even used the ladies.
We had love again that night and next morning we talked more about the
future. Paula brought up the idea of her taking hormones and living full
time as Paula. I told her that I would support her fully of that is what
she choose to do. The issue about work came up and Paula's view on that
was that the company she worked for claimed to be open minded and
supportive of its staff. She told me that she would book sometime with HR
to ask them about company policy.
We did not see each other for a few days after that but we did stay in
contact by mobile and text. She had arranged a meeting with HR for the
following Friday afternoon and was as you can imagine very nervous. We met
again the evening before her meeting. Rather than go out for a meal we had
some Thai delivered. She answered the door as Paula to the delivery person
who in this case was another woman. She did not bat an eyelid and money
and food was exchanged. Over our meal we talked about lots of things but
initially stayed away from the big topic, her meeting the next day.
After we had eaten and cleaned up she broached the subject. We talked at
length about what she should stay and the risk she was taking. The
conversation continued after we went to bed, both of us in short
nightdresses and panties. As we talked she was becoming less nervous. I
raised the question of how she should dress. Paula had arranged to have
the rest of the afternoon off after her meeting as she wanted to attend
the meeting in women's trousers a blouse and some shoes that she had that
were pretty gender neutral.
Mila
- 19.02.2021
- 16
- 0
